Methyl 7-acetyloxy-4a-hydroxy-7-methyl-6-(3-phenylprop-2-enoyloxy)-1-[3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 8487404f-8aef-4b80-9879-c0b65a4b6d2a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 7-acetyloxy-4a-hydroxy-7-methyl-6-(3-phenylprop-2-enoyloxy)-1-[3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2C3C(C(CC3(C(=CO2)C(=O)OC)O)OC(=O)C=CC4=CC=CC=C4)(C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC(=O)OCC1C(C(C(C(O1)OC2C3C(C(CC3(C(=CO2)C(=O)OC)O)OC(=O)C=CC4=CC=CC=C4)(C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C36H42O18/c1-18(37)46-17-25-28(48-19(2)38)29(49-20(3)39)30(50-21(4)40)33(51-25)53-34-31-35(6,54-22(5)41)26(15-36(31,44)24(16-47-34)32(43)45-7)52-27(42)14-13-23-11-9-8-10-12-23/h8-14,16,25-26,28-31,33-34,44H,15,17H2,1-7H3
• InChI Key: YVKBTEHQLJXYOT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₂O₁₈
• Molecular Weight: 762.70 g/mol
• Exact Mass: 762.23711449 g/mol
• Topological Polar Surface Area (TPSA): 232.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.20
• H-Bond Acceptor: 18
• H-Bond Donor: 1
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9779	97.79%
Caco-2	-	0.8451	84.51%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6786	67.86%
OATP2B1 inhibitior	+	0.7052	70.52%
OATP1B1 inhibitior	+	0.7968	79.68%
OATP1B3 inhibitior	+	0.8577	85.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9844	98.44%
P-glycoprotein inhibitior	+	0.8491	84.91%
P-glycoprotein substrate	-	0.5427	54.27%
CYP3A4 substrate	+	0.7178	71.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8881	88.81%
CYP3A4 inhibition	-	0.6982	69.82%
CYP2C9 inhibition	-	0.9189	91.89%
CYP2C19 inhibition	-	0.8961	89.61%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.8068	80.68%
CYP2C8 inhibition	+	0.7925	79.25%
CYP inhibitory promiscuity	-	0.8344	83.44%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5781	57.81%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9093	90.93%
Skin irritation	-	0.6494	64.94%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7006	70.06%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.7540	75.40%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.9043	90.43%
Acute Oral Toxicity (c)	I	0.3925	39.25%
Estrogen receptor binding	+	0.8260	82.60%
Androgen receptor binding	+	0.7116	71.16%
Thyroid receptor binding	+	0.6400	64.00%
Glucocorticoid receptor binding	+	0.7638	76.38%
Aromatase binding	+	0.6080	60.80%
PPAR gamma	+	0.7870	78.70%
Honey bee toxicity	-	0.7581	75.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8717	87.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.95%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.68%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.48%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.62%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.17%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	91.31%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.02%	95.50%
CHEMBL5028	O14672	ADAM10	89.03%	97.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.25%	83.00%
CHEMBL3401	O75469	Pregnane X receptor	88.13%	94.73%
CHEMBL4208	P20618	Proteasome component C5	87.73%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.53%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.41%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.37%	98.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.34%	94.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.28%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.90%	96.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.43%	92.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.55%	93.00%

Plants that contains it

• Duranta erecta

Cross-Links

• PubChem: 163016911
• LOTUS: LTS0229318
• wikiData: Q105365471